Triazine derivatives and herbicidal composition containing the same

ABSTRACT

A pyrimidine or triazine derivative and its salt, said pyrimidine or triazine derivative having the formula: ##STR1## wherein R represents a group of the formula OR 3  {wherein R 3  represents a hydrogen atom, an alkyl group, etc.}, a group of the formula SR 6  {wherein R 6  represents a hydrogen atom, an alkyl group, etc.}, a group of the formula ##STR2## {wherein R 7  and R 8  represent a hydrogen atom, an alkyl group, etc.}, or an imidazolyl group: 
     R 1  represents a hydrogen atom, an alkyl group, etc.; 
     R 2  represents a hydroxyl group, an alkyl group, etc.; 
     A and B represent an alkyl group, etc.; 
     Y represents an oxygen atom, etc.; and 
     Z represents a methine group or a nitrogen atom.

This is a division, of application Ser. No. 07,630,892, filed on Dec.20, 1990, now U.S. Pat. No. 5,118,339.

The present invention relates to novel pyrimidine or triazinederivatives and their salts. More particularly, the present inventionrelates to pyrimidine or triazine derivatives expressed by the generalformula [I] as described below, and also relates to herbicidalcompositions containing said pyrimidine or triazine derivatives or theirsalts as active ingredients, which can be applied to paddy fields,upland fields or non-agricultural fields.

U.S. Pat. No. 4,770,691 (Japanese Unexamined Patent Publication No.174059/1987), U.S. Pat. No. 4,427,437 (Japanese Unexamined PatentPublication No. 55729/1979) and Agr. Biol. Chem., Vol. 30, No. 9, p.896(1966) disclose that 2-phenoxypyrimidine derivatives have herbicidalactivities.

However, the compounds disclosed in these patent specifications andreferences are not always satisfactory in respect of their herbicidaleffects. The present inventors have conducted excessive researches withan aim to develop a further improved compound of the pyrimidine ortriazine type compounds, and have found that the pyrimidine or triazinederivatives having substituents at the specific positions on apyrimidine or triazine ring and a benzene ring exhibit excellentherbicidal activities against not only annular weeds but also perennialweeds and also have a high safety to crop plants, particularly to rice.The present invention has been accomplished on the basis of thesediscoveries.

The present invention provides a pyrimidine or triazine derivative andits salt, said pyrimidine or triazine derivative having the generalformula [I]: ##STR3## wherein R represents a group of the formula OR³{wherein R³ represents a hydrogen atom, an alkyl group, preferably aC₁₋₈ alkyl group, more preferably a C₁₋₄ alkyl group (which may besubstituted with a halogen atom, a nitro group, a cyano group, an alkoxygroup, preferably a C₁₋₈ alkoxy group, more preferably a C₁₋₄ alkoxygroup, an alkylthio group, preferably a C₁₋₈ alkylthio group, morepreferably a C₁₋₄ alkylthio group, an alkylsulfinyl group, preferably aC₁₋₈ alkylsulfinyl group, more preferably a C₁₋₄ alkylsulfinyl group, analkylsulfonyl group, preferably a C₁₋₈ alkylsulfonyl group, morepreferably a C₁₋₄ alkylsulfonyl group, a phenylthio group, aphenylsulfinyl group, a phenylsulfonyl group, a benzyloxy group, anacyloxy group, preferably a R'COO-(R'=C₁₋₈ alkyl), an alkoxycarbonyloxygroup, preferably a C₁₋₈ alkoxycarbonyloxy group, an N,N-dialkylaminogroup, preferably an N,N-di-C₁₋₄ alkylamino group, or a phthalimidoylgroup), an alkenyl group, preferably a C₂₋₈ alkenyl group, ahalogen-substituted alkenyl group, preferably a halogen-substituted C₂₋₈alkenyl group, an alkynyl group, preferably a C₂₋₈ alkynyl group, ahalogen-substituted alkynyl group, preferably a halogen-substituted C₂₋₈alkynyl group, a phenyl group (which may be substituted with a halogenatom, an alkyl group, preferably a C₁₋₆ alkyl group, or an alkoxy group,preferably a C₁₋₆ alkoxy group), a benzyl group (which may besubstituted with a halogen atom, an alkyl group, preferably a C₁₋₈ alkylgroup, or an alkoxy group, preferably a C₁₋₈ alkoxy group), analkylideneamino group, preferably a C₁₋₄ alkylideneamino group, acycloalkylideneamino group, preferably a C₄₋₆ cycloalkylideneaminogroup, a group of the formula ##STR4## {wherein R⁴ represents a hydrogenatom or an alkyl group, preferably a C₁₋₃ alkyl group, R⁵ represents analkyl group, preferably a C₁₋₈ alkyl group, a phenyl group (which may besubstituted with a halogen atom, an alkyl group, preferably a C₁₋₆ alkylgroup, or an alkoxy group, preferably a C₁₋₆ alkoxy group), an aminogroup, an alkylamino group, preferably a C₁₋₈ alkylamino group, or adialkylamino group, preferably a di-C₁₋₄ alkylamino group, n representsan integer of 1 to 3), an alkali metal atom, an alkaline earth metalatom or an organic amine cation}; a group of the formula SR⁶ {wherein R⁶represents a hydrogen atom, an alkyl group, preferably a C₁₋₈ alkylgroup, a phenyl group (which may be substituted with a halogen atom, analkyl group, preferably a C₁₋₆ alkyl group, or an alkoxy group,preferably a C₁₋₆ alkoxy group), a benzyl group (which may besubstituted with a halogen atom, an alkyl group, preferably a C₁₋₆ alkylgroup, or an alkoxy group, preferably a C₁₋₆ alkoxy group), an alkenylgroup, preferably a C₂₋₈ alkenyl group, a halogen-substituted alkenylgroup, preferably a halogen-substituted C₂₋₈ alkenyl group, an alkynylgroup, preferably a C₂₋₈ alkynyl group, or a halogen-substituted alkynylgroup, preferably a halogen-substituted C₂₋₈ alkynyl group}; a group ofthe formula ##STR5## {wherein R⁷ and R⁸ may be the same or different andrepresent a hydrogen atom, an alkyl group, preferably a C₁₋₈ alkylgroup, an alkoxy group, preferably a C₁₋₈ alkoxy group, or a phenylgroup (which may be substituted with a halogen atom, an alkyl group,preferably a C₁₋₆ alkyl group, or an alkoxy group, preferably a C₁₋₆alkoxy group}; or an imidazolyl group; R¹ represents a hydrogen atom, analkyl group, preferably a C₁₋₈ alkyl group (which may be substitutedwith a halogen atom, an alkoxy group, preferably a C₁₋₈ alkoxy group, analkylthio group, preferably a C₁₋₈ alkylthio group, an alkylsulfinylgroup, preferably a C₁₋₈ alkylsulfinyl group, an alkylsulfonyl group,preferably a C₁₋₈ alkylsulfonyl group, an acyl group, preferably anR"CO-- (R"=C₁₋₆ alkyl, phenyl or benzyl), or a cyano group), a phenylgroup (which may be substituted with a halogen atom, an alkyl group,preferably a C₁₋₆ alkyl group, or an alkoxy group, preferably a C₁₋₆alkoxy group) or a benzyl group (which may be substituted with a halogenatom, an alkyl group, preferably a C₁₋₆ alkyl group, or an alkoxy group,preferably a C₁₋₆ alkoxy group); R² represents a hydroxyl group, analkyl group, preferably a C₁₋₈ alkyl group (which may be substitutedwith one or two halogen atoms), an alkoxyalkyl group, preferably a C₂₋₈alkoxyalkyl group, an alkenyl group, preferably a C₂₋₈ alkenyl group, analkynyl group, preferably a C₂₋₈ alkynyl group, an alkoxy group,preferably a C₁₋₈ alkoxy group (which may be substituted with a halogenatom, a benzyloxy group, an alkoxycarbonyl group, preferably a C₁₋₈alkoxycarbonyl group, a cycloalkyl group, preferably a C₃₋₇ cycloalkylgroup, an acyl group, an N,N-dialkylamino group, preferably anN,N-di-C₁₋₄ alkylamino group, or an alkoxy group, preferably a C₁₋₈alkoxy group), a phenyl group (which may be substituted with a halogenatom, an alkyl group, preferably a C₁₋₄ alkyl group, or an alkoxy group,preferably a C₁₋₄ alkoxy group), a phenoxy group (which may besubstituted with a halogen atom, an alkyl group, preferably a C₁₋₄ alkylgroup, or an alkoxy group, preferably a C₁₋₄ alkoxy group), analkenyloxy group, preferably a C₂₋₈ alkenyloxy group (which may besubstituted with one or two halogen atoms or a phenyl group), analkynyloxy group, preferably a C₂₋₈ alkynyloxy group (which may besubstituted with one or two halogen atoms or a phenyl group), abenzyloxy group (which may be substituted with a halogen atom, an alkylgroup, preferably a C₁₋₄ alkyl group, or an alkoxy group, preferably aC₁₋₄ alkoxy group), a trimethylsilyloxy group, a cycloalkoxy group,preferably a C₃₋₇ cycloalkoxy group, a group of the formula ##STR6##{wherein R⁹ represents an alkyl group, preferably a C₁₋₈ alkyl group(which may be substituted with a halogen atom), a cycloalkyl group(which may be substituted with a halogen atom, an alkyl group,preferably a C₁₋₄ alkyl group, or an alkoxy group, preferably a C₁₋₄alkoxy group), an alkoxy group, preferably a C₁₋₈ alkoxy group, or agroup of the formula: (wherein R⁷ and R⁸ are the same as definedabove)}, a group of the formula ##STR7## (wherein X represents a halogenatom, an alkyl group, preferably a C₁₋₄ alkyl group, or an alkoxy group,preferably a C₁₋₄ alkoxy group, n represents an integer of 1 to 3 and R⁴is the same as defined above), a phenylamino group, analkoxycarbonylamino group, preferably a C₁₋₄ alkoxycarbonylamino group,or an alkylcarbonylamino group, preferably a C₁₋₄ alkylcarbonylaminogroup; A and B may be the same or different and represent an alkylgroup, preferably a C₁₋₄ alkyl group, an alkoxy group, preferably a C₁₋₄alkoxy group, a halogen atom, a halogen-substituted alkyl group,preferably a halogen-substituted C₁₋₄ alkyl group, a halogen-substitutedalkoxy group, preferably a halogen-substituted C₁₋₄ alkoxy group, or adialkylamino group, preferably a di-C₁₋₄ alkylamino group; Y representsan oxygen atom, a sulfur atom, an -NH- group or a group of the formula##STR8## (wherein R¹⁰ represents a hydrogen atom, an alkyl group,preferably a C₁₋₈ alkyl group, or an alkoxy group, preferably a C₁₋₈alkoxy group); and Z represents a methine group or a nitrogen atom.

Typical examples of the compound expressed by the general formula [I] ofthe present invention are listed in the following Table 1.

    TABLE 1      ##STR9##      (I)          Physical properties:         Melting point Com-     (°C.) or Re- pound        fractive index No. R R.sup.1 R.sup.2 A     B Y Z (n.sub.D      .sup.20)                                                     1 OH     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 125-127  2 OH CH.sub.3     OC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 O CH 113-115  3 OH CH.sub.3     OC.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 O CH 1.5380      4     ##STR10##      CH.sub.3 OCH.sub.3 OCH.sub. 3 OCH.sub.3 O CH 1.5545      5     ##STR11##      CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 O CH 80-82      6     ##STR12##      CH.sub.3 OC.sub.3 H.sub.7 -i OCH.sub.3 OCH.sub.3 O CH 1.5472   7      ##STR13##      CH.sub.3      ##STR14##      OCH.sub.3 OCH.sub.3 O CH 1.5817   8 OCH.sub.3 CH.sub.3 OH OCH.sub.3     OCH.sub.3 O CH 131-132  9 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3     OCH.sub.3 O CH 105-106 10 OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3     OCH.sub.3 O CH unmeasurable 11 OCH.sub.3 CH.sub.3 OC.sub.2 H.sub.5     OCH.sub.3 OCH.sub.3 O CH 93-95 12 OCH.sub.3 CH.sub.3 OC.sub.3 H.sub.7 -i     OCH.sub.3 OCH.sub.3 O CH 74-75      13 OCH.sub.3 CH.sub.3     ##STR15##      OCH.sub.3 OCH.sub.3 O CH 1.5681  14 OCH.sub.3 CH.sub.3 OCH.sub.2     CHCH.sub.2 OCH.sub.3 OCH.sub.3 O CH 76-78 15 OC.sub.2 H.sub.5 CH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 65-68 16 OC.sub.3 H.sub.7 CH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5449 17 OC.sub.3 H.sub.7 -i     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5301 18 OH H OCH.sub.3     OCH.sub.3 OCH.sub.3 O CH   109-111.5 19 OCH.sub.3 H OH OCH.sub.3     OCH.sub.3 O CH 1.5558 20 OCH.sub.3 H OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH     78-79 21 OCH.sub.3 H OC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 O CH 1.5582     22 OCH.sub.3 H      ##STR16##      OCH.sub.3 OCH.sub.3 O CH 1.5261      23 OCH.sub.3 H     ##STR17##      OCH.sub.3 OCH.sub.3 O CH 1.5799      24 OCH.sub.3 H     ##STR18##      OCH.sub.3 OCH.sub.3 O CH unmeasurable  25 OCH.sub.3 H NHCOOCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 108-109 26 OCH.sub.3 H NHCOOC.sub.2 H.sub.5     OCH.sub.3 OCH.sub.3 O CH 136-138 27 OCH.sub.3 H NHCOCH.sub.3 OCH.sub.3     OCH.sub.3 O CH 144-146      28 OCH.sub.3 H     ##STR19##      OCH.sub.3 OCH.sub.3 O CH 122-124  29 OC.sub.2 H.sub.5 H OCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 1.5449 30 OC.sub.3 H.sub.7 -i H OCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 1.5450 31 OCH.sub.2 (CH.sub.2).sub.2 CH.sub.2     OCH.sub.3 H OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5430      32     ##STR20##      H OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5741  33 OCH.sub.3 CH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 S CH 1.5709 34 OCH.sub.3 CH.sub.3 OC.sub.2     H.sub.5 OCH.sub.3 OCH.sub.3 S CH 62.5-64      35 OCH.sub.3 H     ##STR21##      OCH.sub.3 OCH.sub.3 O CH 1.5849  36 OCH.sub.3 CH.sub.3 OCH.sub.3 Cl     OCH.sub.3 O CH 110-113 37 OCH.sub.3 CH.sub.3 OCH.sub.3 Cl CH.sub.3 O CH     1.5587 38 OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 OCH.sub.3 O CH 126-129     39 OCH.sub.3 CH.sub.3 OCH.sub.3 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 O CH     1.5342 40 OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 CH.sub.3 O CH 79-80 41     OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O N 131-135  42      ##STR22##      CH.sub.3      ##STR23##      OCH.sub.3 OCH.sub.3 O CH 1.5740  43 OCH.sub.3 CH.sub.3 OC.sub.3 H.sub.7     OCH.sub.3 OCH.sub.3 O CH 73-76      44     ##STR24##      CH.sub.3 OC.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3 O CH 65-66  45 OH     CH.sub.3 OC.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3 O CH 1.5112 46 OCH.sub.3     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 NH CH 82-84 47 OCH.sub.3 CH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 NH CH 139-141 48 OCH.sub.2 OC.sub.2     H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5290 49 ONa     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 138-150 50 OCH.sub.3     CH.sub.3 OCH.sub.3 OCH.sub.3 OCHF.sub.2 O CH 1.5221  51 OCH.sub.3     CH.sub.3      ##STR25##      OCH.sub.3 OCH.sub.3 O CH 1.5823      52 OCH.sub.3 CH.sub.3     ##STR26##      OCH.sub.3 OCH.sub.3 O CH 1.5290  53 OCH.sub.3 C.sub.2 H.sub.5 OCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 75-77 54 OCH.sub.3 C.sub.3 H.sub.7 OCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 1.5343 55 OCH.sub.3 C.sub.3 H.sub.7      -i OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH      56 OCH.sub.3     ##STR27##      OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH               57 OCH.sub.3     ##STR28##      OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH            58 OCH.sub.3 CH.sub.3     OCH.sub.2 C*CH OCH.sub.3 OCH.sub.3 O CH   77-80.5  59 OCH.sub.3 CH.sub.3      ##STR29##      OCH.sub.3 OCH.sub.3 O CH  60 OCH.sub.3 CH.sub.3 OC.sub.4 H.sub.9     OCH.sub.3 OCH.sub.3 O CH 1.5374      61 OCH.sub.3 CH.sub.3     ##STR30##      OCH.sub.3 OCH.sub.3 O CH 1.5772      62 OCH.sub.3 CH.sub.3     ##STR31##      OCH.sub.3 OCH.sub.3 O CH 109-111  63 OH CH.sub.3 OC.sub.2 H.sub.5     OCH.sub.3 OCH.sub.3 S CH 152-155 64 OH CH.sub.3 OCH.sub.3 OCH.sub.3     OCH.sub.3 S CH 144-147      65     ##STR32##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5687      66     ##STR33##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  67 OCH.sub.2 CN CH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5376 68 OCH.sub.2 OCH.sub.3     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5408 69 OCH.sub.2      OCOC.sub.4 H.sub.9 -t CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH     1.5248 70 OCH(CH.sub.3)OCOOC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 OCH.sub.3     OCH.sub.3 O CH 1.5220      71     ##STR34##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5589      72     ##STR35##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 170-172      73 ONC(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH     1.5355 74 ONC(C.sub.2 H.sub.5).sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3     OCH.sub.3 O CH 103-105 75 OCH.sub.2 C*CH CH.sub.3 OCH.sub.3 OCH.sub.3     OCH.sub.3 O CH 95-98 76 OCH.sub.2      CHCH.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5465 77     OCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 N(CH.sub.3).sub.2 O CH 78     OCH.sub.3 CH.sub.3 OCH.sub.2 CClCH.sub.2 OCH.sub.3 OCH.sub.3 O CH 54-56     79 OCH.sub.3 CH.sub.3 OCH.sub.2 CClCHCl OCH.sub.3 OCH.sub.3 O CH 1.5468     80 OCH.sub.3 CH.sub.3 OCH.sub.2 CClCHCl OCH.sub.3 OCH.sub.3 O CH 1.5510     81 OCH.sub.3 CH.sub.3 OCH.sub.2 OC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 O     CH 1.5210      82 OCH.sub.3 CH.sub.3     ##STR36##      OCH.sub.3 OCH.sub.3 O CH 1.5373  83 OCH.sub.3 CH.sub.3 OCOCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 1.5510 84 OCH.sub.3 CH.sub.3 OCOC.sub.4 H.sub.9     -t OCH.sub.3 OCH.sub.3 O CH 1.5291      85 OCH.sub.3 CH.sub.3     ##STR37##      OCH.sub.3 OCH.sub.3 O CH 94-96      86 OCH.sub.3 CH.sub.3     ##STR38##      OCH.sub.3 OCH.sub.3 O CH 121-125      87 OCH.sub.3 CH.sub.3     ##STR39##      OCH.sub.3 OCH.sub.3 O CH 1.5377  88 OCH.sub.3 CH.sub.3 OCOOCH.sub.3     OCH.sub.3 OCH.sub.3 O CH 122-126      89 OCH.sub.3 CH.sub.3     ##STR40##      OCH.sub.3 OCH.sub.3 O CH 1.5508  90 OCH.sub.3 CH.sub.3 OCH.sub.2 Cl     OCH.sub.3 OCH.sub.3 O CH 91 OCH.sub.3 CH.sub.3 O(CH.sub.2).sub.2 Cl     OCH.sub.3 OCH.sub.3 O CH 1.5540 92 OCH.sub.3 CH.sub.3 O(CH.sub.2).sub.3     Cl OCH.sub.3 OCH.sub.3 O CH 1.5539 93 OCH.sub.3 CH.sub.3 OCH.sub.2     C(Br)CH.sub.2 OCH.sub.3 OCH.sub.3 O CH 1.5576  94 OCH.sub.3 CH.sub.3      ##STR41##      OCH.sub.3 OCH.sub.3 O CH 1.5438  95 OCH.sub.3 CH.sub.3 OCH.sub.2     CHCHCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5520 96 OCH.sub.3 CH.sub.3     OCH.sub.2 CH.sub.2 CHCH.sub.2 OCH.sub.3 OCH.sub.3 O CH 1.5473 97     OCH.sub.3 CH.sub.3 OCOC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 O CH 98     OCH.sub.3 CH.sub.3 OCOC.sub.3 H.sub.7 OCH.sub.3 OCH.sub.3 O CH 99     OCH.sub.3 CH.sub.3 OCOCH.sub.2 Cl OCH.sub.3 OCH.sub.3 O CH 100       OCH.sub.3 CH.sub.3 OCOOC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 O CH 101     OCH.sub.3 CH.sub.3 OCON(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 O CH 102     OCH.sub.3 CH.sub.3 OCOCF.sub.3 OCH.sub.3 OCH.sub.3 O CH 110-111 103     OCH.sub.3 CH.sub.3 OCH.sub.2 C(CH.sub.3)CH.sub.2 OCH.sub.3 OCH.sub.3 O     CH 1.5496  104       OCH.sub.3 CH.sub.3     ##STR42##      OCH.sub.3 OCH.sub. 3 O CH 1.5572  105  OCH.sub.3 CH.sub.3 OCH.sub.2     CHCHCl OCH.sub.3 OCH.sub.3 O CH 1.5588 106  OCH.sub.3 CH.sub.3 OCH.sub.2     CHCCl.sub.2 OCH.sub.3 OCH.sub.3 O CH 1.5579 107  OCH.sub.3 CH.sub.3     OCH.sub.2 CF.sub.3 OCH.sub.3 OCH.sub.3 O CH 108  OCH.sub.3 CH.sub.3     OC(CH.sub.3).sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5339 109  OCH.sub.3     CH.sub.3 OSi(CH.sub.3).sub.3 OCH.sub.3 OCH.sub.3 O CH  110  OCH.sub.3     CH.sub.3      ##STR43##      OCH.sub.3 OCH.sub.3 O CH  111  OCH.sub.3 CH.sub.3 OCH.sub.2      CHC(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 O CH 1.5341 112  OCH.sub.3     CH.sub.3 OC.sub.4 H.sub.9 -s OCH.sub.3 OCH.sub.3 O CH 1.5407  113     OCH.sub.3 CH.sub.3      ##STR44##      OCH.sub.3 OCH.sub.3 O CH  114       OCH.sub.3 CH.sub.3     ##STR45##      OCH.sub.3 OCH.sub.3 O CH   115       OCH.sub.3 CH.sub.3     ##STR46##      OCH.sub.3 OCH.sub.3 O CH  116       OCH.sub.3 CH.sub.3     ##STR47##      OCH.sub.3 OCH.sub.3 O CH 1.5724  117       OCH.sub.3 CH.sub.3     ##STR48##      OCH.sub.3 OCH.sub.3 O CH  118       OCH.sub.3 CH.sub.3     ##STR49##      OCH.sub.3 OCH.sub.3 O CH 158-162  119       OCH.sub.3 CH.sub.3     ##STR50##      OCH.sub.3 OCH.sub.3 O CH 112-115  120       OCH.sub.3 CH.sub.3     ##STR51##      OCH.sub.3 OCH.sub.3 O CH 169-171  121       OCH.sub.3 CH.sub.3     ##STR52##      OCH.sub.3 OCH.sub.3 O CH 133-135  122  OCH.sub.3 CH.sub.3 C.sub.3     H.sub.7 OCH.sub.3 OCH.sub.3 O CH 108-112 123  OCH.sub.3 CH.sub.3 C.sub.     2 H.sub.5 OCH.sub.3 OCH.sub.3 O CH 124  OCH.sub.3 CH.sub.3 C.sub.3     H.sub.7 -i OCH.sub.3 OCH.sub.3 O CH 125  OCH.sub.3 CH.sub.3 C.sub.4     H.sub.9 OCH.sub.3 OCH.sub.3 O CH 126  OCH.sub.3 CH.sub.3 C.sub.4 H.sub.9     -t OCH.sub.3 OCH.sub.3 O CH 127  OCH.sub.3 CH.sub.3 C.sub.2 H.sub.4     OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 128  OCH.sub.3 CH.sub.3 CH.sub.2     CHCH.sub.2 OCH.sub.3 OCH.sub.3 O CH 129  OH CH.sub.3 OC.sub.3 H.sub.7 -i     OCH.sub.3 OCH.sub.3 S CH 164-168 130  OH CH.sub.3 OCH.sub.2 CHCH.sub.2     OCH.sub.3 OCH.sub.3 S CH 123-125 131  OCH.sub.3 CH.sub.3 OCH.sub.3     OCH.sub.3 OCH.sub.3 NCHO CH 147-149 132  OCH.sub.3 CH.sub.3 OCH.sub.3     OCH.sub.3 OCH.sub.3 NCOCH.sub.3 CH   100-102.5 133  OCH.sub.3 CH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 NCOOCH.sub.3 CH 95-97 134  OCH.sub.3 H     OCH.sub.3 OCH.sub.3 OCH.sub.3 S CH 135  OCH.sub.3 H OC.sub.2 H.sub.5     OCH.sub.3 OCH.sub.3 S CH  136      ##STR53##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 118-121  137      ##STR54##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 194-199  138  SCH.sub.3     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 139  SC.sub.2 H.sub.5     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 73-88  140      ##STR55##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  141      ##STR56##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  142      ##STR57##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  143      ##STR58##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  144      ##STR59##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  145      ##STR60##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  146      ##STR61##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5491  147      ##STR62##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  148      ##STR63##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  149  NHC.sub.2 H.sub.5     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 150  NHC.sub.3 H.sub.7     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH   103-104.5  151      ##STR64##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH unmeasurable  152       OCH.sub.2 COCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH     1.5329  153      ##STR65##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 118-121  154  OCH.sub.2     SCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5459  155      ##STR66##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  156  OCH.sub.2 NO.sub.2     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 157  O(CH.sub.2).sub.2 Cl     CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH unmeasurable 158  OCH.sub.2     CF.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  159      ##STR67##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  160  OCH.sub.3 CH.sub.3     OCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 O N 1.5378 161  OCH.sub.3 CH.sub.2     Cl OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 162  OCH.sub.3 CH.sub.2 Br     OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 163  OCH.sub.3 CH.sub.2 OCH.sub.3     OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 164  OCH.sub.3 CH.sub.2 OC.sub.2     H.sub.5 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 1.5210 165  OCH.sub.3     CH.sub.2 SCH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 166  OCH.sub.3     CH.sub.2 SC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 167     OCH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  168  OCH.sub.3     CH.sub.3      ##STR68##      OCH.sub.3 OCH.sub.3 O CH  169      ##STR69##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  170      ##STR70##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  171      ##STR71##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  172  OCH.sub.2 C*CCH.sub.2     Cl CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  173       OCH.sub.3     ##STR72##      OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH   174       OCH.sub.3     ##STR73##      OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  175       OCH.sub.3     ##STR74##      OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  176       OCH.sub.3 CH.sub.3     ##STR75##      OCH.sub.3 OCH.sub.3 O CH  177       OCH.sub.3 CH.sub.3     ##STR76##      OCH.sub.3 OCH.sub.3 O CH  178  OCH.sub.3 CH.sub.3 OCH.sub.2 C*CCH.sub.2     Cl OCH.sub.3 OCH.sub.3 O CH  179      ##STR77##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  180      ##STR78##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH  181  OCH.sub.3 CH.sub.3     OCH.sub.3 CF.sub.3 OCH.sub.3 O CH  182      ##STR79##      CH.sub.3 OCH.sub.3 OCH.sub.3 OCH.sub.3 O CH 121-125  183  OCH.sub.3     CH.sub.3      ##STR80##      OCH.sub.3 OCH.sub.3 O CH 1.5402     Note:     Compound No. 9 and Compound No. 10 are structural isomers each other.     Compound No. 46 and Compound No. 47 are structural isomers each other.     Compound No. 79 and Compound No. 80 are structural isomers each other.     * = Triple bond

The compound of the present invention can be prepared, for example, bythe following Processes A to F. ##STR81## (wherein R, R¹, R², A, B, Zand Y are as defined above, and HD represents an acid for forming a saltwith an amine, for example a corresponding acid for forming sulfate,hydrochloride or the like.)

The compound of the general formula [I] of the present invention can beprepared by reacting the compound of the general formula [II] with thecompound of the general formula [III] in the presence of a base in aninert solvent at a temperature in the range from 0° C. to the boilingpoint of the solvent for 30 minutes to 12 hours. As the base, acarbonate, hydrogencarbonate, acetate, alcholate, hydroxide, hydride oroxide of an alkali metal such as sodium and potassium or of an alkalineearth metal such as magnesium and calcium, may be employed. In addition,an organic base, for example, pyridine or tertiary amine such astriethylamine, may be employed.

As the solvent, a hydrocarbon solvent such as toluene, benzene, xyleneor the like, a halogenated hydrocarbon solvent such as methylenechloride, chloroform or the like, an alcohol solvent such as methanol,ethanol or the like, an ether solvent such as ethyl ether, isopropylether, tetrahydrofuran, 1,4-dioxane or the like, an aprotic polarsolvent such as N,N-dimethylformamide, N,N-dimethylacetamide,dimethylsulfoxide or the like, and an ester solvent such as ethylacetate or the like, may be employed.

Preferable combination examples of a solvent and a base include thecombination of methanol and potassium acetate and the combination ofchloroform and triethylamine.

Process B

The compound of the general formula [I] of the present invention mayalso be prepared by reacting the compound of the general formula [II]with an amine of the general formula [IV], such as hydrazines, anilines,hydroxyamines or the like, preferably in a solvent, as shown in thefollowing reaction formula: ##STR82## (wherein R, R¹, R², A, B, Y and Zare as defined above).

The solvent and the reaction temperature used in this process may be thesame as those employed in the above-mentioned Process A. One of thepreferable reaction conditions includes a refluxing in methanol solvent.

The compounds of the general formula [II] used as a starting material inthe above Processes A and B is also a novel compound, and can beprepared as illustrated in the following reaction formulas.

(a) The compound of the general formula [II] wherein Y is an oxygen atomor a sulfur atom: ##STR83## (wherein Y¹ is an oxygen atom or a sulfuratom, and R, R¹, A, B and Z are as defined above, L representing aneliminating group).

That is, the compound of the general formula [II-1] can be prepared byreacting the compound of the general formula [V] with the compound ofthe general formula [VI] in the presence of a base in an inert solventat a temperature in the range from 0° C. to the boiling point of thesolvent. The base and the solvent used in this process may be the sameas those described above. Preferable combination examples of the solventand the base include the combination of dimethylformamide and potassiumcarbonate or the combination of dimethylformamide and sodium hydride.

The compound of the general formula [V] is well known, and can beprepared, for example, in accordance with the process described in thePharmaceutical Journal, Vol. 74, p.466 (1954).

The compound of the general formula [V] may also be prepared inaccordance with the following two synthesis routes as illustrated by thefollowing reaction formulas: ##STR84## (wherein Q represents an alkylgroup, an alkoxyalkyl group or a benzyl group, and R and R¹ are asdefined above).

The acylphenone derivative of the general formula (1) is acetalized withethylene glycol in the presence of a Lewis acid to obtain the compoundof the general formula (2). The compound of the general formula (2) isthen reacted with carbon dioxide in the presence of an organic metalsuch as n-butyl lithium or phenyl lithium in an inert solvent such asn-hexane, toluene or benzene to obtain the compound of the generalformula (3). The resultant compound is then esterified by normal method,and the protecting groups of acetal and hydroxyl groups are theneliminated in order or simultaneously to obtain the aimed product. Thecompound of the general formula (4) may also be prepared by reacting thecompound of the general formula (2) with a halo-formic acid ester in thepresence of an organic metal such as n-butyl lithium or phenyl lithiumin an inert solvent such as n-hexane, toluene or benzene. ##STR85##(wherein R, R¹ and Q are as defined above).

The phthalide derivative of the general formula (7) is hydrolyzed underoxidation condition in the presence of potassium permanganate andmagnesium nitrate to obtain the salicylic acid derivative of the generalformula (8).

The resultant compound is then esterified by normal method, and theprotecting group of a hydroxyl group is selectively eliminated to obtainthe aimed compound.

The compound of the general formula [V] wherein Y¹ is a sulfur atom canbe prepared from the compound of the general formula [VII] disclosed inthe above reference as illustrated in the following reaction formula:##STR86## (wherein R and R¹ are as defined above). (b) The compound ofthe general formula [II] wherein Y represents an --NH-- group or an##STR87## group: ##STR88## (wherein R, R¹ , A, B, Z and L are as definedabove).

That is, the amino group of the anthranylic acid derivative of thegeneral formula [VII] disclosed in the above reference is formylatedwith formic acid to obtain the compound of the general formula [VIII].The resultant compound is reacted with the pyrimidine or triazinederivative of the general formula of [VI] to obtain the anthranylic acidderivative of the general formula [II-2]. In this case, the reactionconditions including solvent, base, reaction temperature and reactiontime used in this process are the same as those used in Process A. Theresultant compound may further be deformylated to obtain the compound ofthe general formula [II-3].

Process C

The compound of the present invention may also be prepared by alkylatingthe corresponding oxime with an alkylating agent as illustrated in thefollowing reaction formula. Examples of the alkylating agent includealkyl halide, alkenyl halide, benzyl halide, halogen-substitutedaliphatic acid ester, cycloalkyl halide, alkyl sulfate or the like.##STR89## (wherein R, R¹, A, B, Y and Z are as defined above, and R¹¹represents an alkyl group, a phenyl group, an alkenyl group, an alkynylgroup, a benzyl group, an alkoxycarbonylalkyl group or a cycloalkylgroup, L representing an eliminating group).

The compound of the formula [IX] can be prepared, for example, byreacting the compound of the general formula [II] with the hydroxyaminesalt of the general formula [X] in the same manner as in the aboveProcess A. ##STR90## (wherein R, R¹, A, B, Z, Y and HD are as definedabove).

Process D

The compound of the present invention may also be prepared by reactingthe compound of the general formula [XI] with the compound of thegeneral formula [VI] in the presence of a base in an inert solvent at atemperature in the range from 0° C. to the boiling point of the solvent.The base and the solvent used in this process may be the same as thoseused in the synthesis of the material of the general formula [II] inaccordance with Process A. ##STR91## (wherein R, R¹, A, B, Y¹, Z and Lare as defined above).

The compound of the general formula [XI] which is the starting materialof the above reaction is also a novel compound, and can be prepared, forexample, by reacting the compound of the formula [V] disclosed in theabove reference with the amine salt of the formula [III] in the samemanner as in Process A in accordance with the following reactionformula: ##STR92## (wherein R, R¹, R², Y and HD are as defined above).

Process E

The compound of the present invention having the general formula [I]wherein R is hydroxy group can be obtained by catalyticallyhydrogen-reducing the compound of the general formula [I] wherein R is abenzyloxy group, in the presence of a catalyst such as Raney nickel,palladium carbon or the like. ##STR93## (wherein R¹, R², A, B, Y and Zare as defined above).

Process F

The compound of the present invention may also be prepared asillustrated in the following reaction formula: ##STR94## (wherein, R,R¹, R², A, B, Z, Y and L are as defined above).

For example, the compound of the present invention can also be preparedby condensing a benzoic acid derivative obtained by Process E with anester residue having a corresponding eliminating group in the presenceof a suitable base such as potassium carbonate, sodium hydride or thelike in a suitable inert solvent such as dimethylformamide,tetrahydrofuran, acetonitrile, toluene or the like, at a temperature inthe range from room temperature to 100° C.

Typical examples of intermediate products having the general formula[II] or [XI] for the compounds of the present invention are listed inthe following Tables 2-1 and 2-2.

These intermediate products also have excellent herbicidal activitiesand selectivities.

                                      TABLE 2-1                                   __________________________________________________________________________     ##STR95##                                (II)                                Inter-                             Physical properties:                       mediate                            Melting point (°C.)                 compound                           or Refractive index                        No.   R         R.sup.1                                                                          A    B    Y  Z  (n.sub.D .sup.20)                          __________________________________________________________________________     1    OH        CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH 163-165                                     2                                                                                   ##STR96##                                                                              CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH 141-143                                     3    OCH.sub.3 CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH 164-166                                     4    OC.sub.2 H.sub.5                                                                        CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                             5    OC.sub.3 H.sub.7                                                                        CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH 84.5-86                                     6    OC.sub. 3 H.sub.7 -i                                                                    CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                             7    OCH.sub.3 CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          S  CH 149-151                                     8    OCH.sub.3 CH.sub.3                                                                         Cl   OCH.sub.3                                                                          O  CH 117.5-120                                   9    OCH.sub.3 CH.sub.3                                                                         Cl   CH.sub.3                                                                           O  CH 109-112                                    10    OCH.sub.3 CH.sub.3                                                                         CH.sub.3                                                                           OCH.sub.3                                                                          O  CH 127-130                                    11    OCH.sub.3 CH.sub.3                                                                         OC.sub.2 H.sub.5                                                                   OC.sub.2 H.sub.5                                                                   O  CH   117-118.5                                12    OCH.sub.3 CH.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                           O  CH 138-140                                    13    OCH.sub.3 CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          O  N  151-156                                    14    OCH.sub.3 CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          NH CH 108-110                                    15    OCH.sub.3 CH.sub.3                                                                         OCHF.sub.2                                                                         OCH.sub.3                                                                          O  CH 70-73                                      16    OH        CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          S  CH 177-180                                    17    OCH.sub.3 C.sub.2 H.sub.5                                                                  OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH 120-122                                    18    OCH.sub.3 H  OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH 91-93                                      19    OCH.sub.3 CH.sub.3                                                                          ##STR97##                                                                         OCH.sub.3                                                                          O  N  145-149                                    20    OCH.sub.3 CH.sub.3                                                                          ##STR98##                                                                         OCH.sub.3                                                                          O  CH                                            __________________________________________________________________________

                  TABLE 2-2                                                       ______________________________________                                         ##STR99##                    (XI)                                                                                  Physical                                Inter-                                properties:                             mediate                               Melting point                           com-                                  (°C.) or                         pound                                 Refractive                              No.    R       R.sup.1                                                                              R.sup.2     Y.sup.1                                                                           index (n.sub.D .sup.20)                 ______________________________________                                        21     OCH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3   O   1.5423                                  22     OH      CH.sub.3                                                                             OCH.sub.3   O   79-81                                   23     OCH.sub.3                                                                             CH.sub.3                                                                              ##STR100## O                                           24     OCH.sub.3                                                                             CH.sub.3                                                                              ##STR101## O                                           25     OCH.sub.3                                                                             C.sub.2 H.sub.5                                                                      OCH.sub.3   O                                           ______________________________________                                    

Now, a process for preparing the compound of the present invention andits intermediate product will be described in further detail withreference to Examples and Reference Examples. However, it should beunderstood that the present invention is by no means restricted to suchspecific Examples.

EXAMPLE 1 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(N-methoxyimino)ethyl]benzoateCompound No. 9)

5 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate(melting point=164° to 166° C.), 3 g of methanolamine hydrochloride and3.6 g of triethylamine were added to 50 ml of chloroform, and themixture was reacted with stirring for 8 hours under refluxing. Thereaction liquor was poured into a large amount of water, and thechloroform layer was separated out after washing with water, the solventbeing then distilled off under reduced pressure after drying. An oilyproduct was purified by column chromatography using hexane/isopropylether as a developing solvent, and was recrystallized in ahexane/isopropyl ether mixture solvent to obtain 3.2 g of the aimedcompound of a colorless transparent prism-like crystal (meltingpoint=105° to 106° C.) at a yield of 50%.

EXAMPLE 2 Preparation of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-[N-methoxyimino)ethyl]benzoate (Compound No. 9)

3 3 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate,4.1 g of methanolamine hydrochloride and 4.9 g of potassium acetate wereadded to 50 ml of methanol, and the mixture was reacted with stirringfor 2 hours under refluxing by heating. The reaction liquor was pouredinto a large amount of water, and the product was extracted with ethylacetate after being made acidic with hydrochloric acid, the productbeing washed with sodium hydrogencarbonate aqueous solution and water insequence. After drying, the concentrated crystal thus obtained waswashed with isopropyl ether to obtain 3.2 g of the aimed product(melting point=105° to 106° C.) at a yield of 89%.

REFERENCE EXAMPLE 1 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoate (Intermediateproduct No. 7)

10.2 g of 2-amino-6-acetylbenzoic acid was converted into a diazoniumsalt with a mixture of 14.2 ml of concentrated hydrochloric acid, 40 mlof water and 4.3 g of sodium nitrite, and the diazonium salt wasgradually added dropwise at a temperature of 0° to 5° C. to a sodiumdisulfide aqueous solution (prepared from 14.3 g of sodium sulfide.9H₂O, 1.9 g of sulfur, 4.6 g of sodium hydroxide and 30 ml of water). Afteradding dropwise, the reaction liquor was stirred for 2 hours at roomtemperature to complete the reaction. The reaction liquor was pouredinto a large amount of water, and after adding concentrated hydrochloricacid thereto, the product was extracted with ethyl acetate. To the ethylacetate layer, was added sodium hydrogencarbonate aqueous solution, andthe content soluble in sodium hydrogencarbonate was extracted. To theresultant aqueous solution, was added 14.8 g of sodium pyrosulfate, andthe mixture was refluxed for 30 minutes to complete the reaction. To thereaction liquor, was added concentrated hydrochloric acid, and theproduct was extracted with ethyl acetate. The extracted liquor wasdried, and the solvent was distilled off under reduced pressure toobtain 10.1 g of.2-mercapto-6-acetylbenzoic acid at a yield of 90%.

10.1 g of 2-mercapto-6-acetylbenzoic acid thus obtained and 7.6 g ofpotassium hydroxide were then dissolved in a mixed solvent of 20 ml ofwater and 30 ml of N,N-dimethylformamide. To the resultant solution, wasadded 13.5 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and theresultant solution was reacted with stirring at room temperature for 2hours and further at 60° C. for 0.5 hour. The reaction liquor was thenpoured into a large amount of water, and the neutral content wasextracted with chloroform. Concentrated hydrochloric acid was added tothe water layer, and an oily product thus precipitated was extractedwith ether and then dried. The ether solution was then passed through ashort column of Florisil, and ether was distilled off to obtain 6.1 g of2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoic acid.

After suspending 0.3 g of 60% sodium hydride in 40 ml of a 1:1 mixedsolvent of tetrahydrofuran and N,N-dimethylformamide, 2.5 g of the aboveobtained 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoic acid wasadded to the suspension, and was stirred for 30 minutes. 1.3 g of methyliodide was added dropwise to the resultant liquor at room temperature,and the resultant liquor was refluxed by heating for 2 hours to completethe reaction. The reaction liquor was then poured into water, and wasextracted with ethyl acetate. The extracted liquor was washed with waterand dried to distill off the solvent under reduced pressure. The residuethus obtained was purified by chromatography to obtain 5.8 g of theaimed compound (melting point=149 to 151° C.) at a yield of 32%.

EXAMPLE 3 Preparation: of methyl2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-[1-(N-methoxyimino)ethyl]benzoate(Compound No. 33)

1.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)thio]-6-acetylbenzoateand 0.5 g of methoxyamine hydrochloride were dissolved in 6 ml ofmethanol, and the resultant solution was refluxed for 15 minutes. Aftercooling the mixed liquor to room temperature, 0.8 g of potassiumcarbonate was added to this liquor and the resultant liquor washeat-refluxed for 3 hours. The reaction liquor was poured into a largeamount of water, and an oily product thus precipitated was extractedwith ethyl acetate. The ethyl acetate layer was washed with water, andwas dried to distill off ethyl acetate under reduced pressure. Theresidue thus obtained was purified by chromatography to obtain 0.65 g ofthe aimed compound (refractive index=1.5709) at a yield of 59%.

EXAMPLE 4 Preparation of methyl2-[[4,6-dimethoxypyrimidin-2-yl)oxy]-6-(N'-acetylhydrazomethyl)benzoate(Compound No. 27)

0.7 g of methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate,0.7 g of acetyl hydrazine and 10 ml of methanol were placed in a 50 mleggplant type flask, and were stirred for 30 minutes at roomtemperature. Methanol was distilled off under reduced pressure, and theresidue was dissolved in ethyl acetate. The organic layer was washedwith water, 5% hydrochloric acid and a saturated salt aqueous solution,and was dried with magnesium sulfate anhydride. After filtering, a smallamount of Florisil was added to the resultant product, and was stirredfor 5 minutes. The Florisil was filtered out, and ethyl acetate wasdistilled off under reduced pressure. The solid product thus obtainedwas washed with isopropyl ether to obtain 0.7 g of the aimed compound(melting point=144° to 146° C.) at a yield of 85%.

REFERENCE EXAMPLE 2 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate (Intermediateproduct No. 18)

13.8 g of potassium carbonate and 50 ml of DMF were placed in a 200 mleggplant type flask, and 11.1 g of methyl 2-formyl-6-hydroxybenzoate and14.6 g of 4,6-dimethoxy-2-methanesulfonylpyrimidine were added theretowith stirring. The mixture was stirred at 80° C. for 1 hour, and theresultant liquor was poured into an ice water after cooling. An oilyproduct thus precipitated was extracted with ethyl acetate, and wasdried with magnesium sulfate anhydride. Ethyl acetate was distilled offunder reduced pressure, and the residue thus obtained was purified bycolumn chromatography to obtain 11.0 g of the aimed compound (meltingpoint=91° to 93° C.) at a yield of 52%.

EXAMPLE 5 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl]oxy]-6-(N'-phenylhydrazomethyl)benzoate(Compound No. 24)

0.9 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate,0.7 g of phenylhydrazine hydrochloride, 0.4 g of potassium acetate and10 ml of methanol were placed in a 50 ml eggplant type flask, and werestirred for 10 minutes at room temperature. Methanol was distilled offunder reduced pressure, and the residue was dissolved in ethyl acetate.The organic layer was washed with water, 5% hydrochloric acid and asaturated salt aqueous solution, and was dried with magnesium sulfateanhydride. After filtering, a small amount of Florisil was added to theresultant product, and the resultant product was stirred for 5 minutes.The Florisil was filtered out, and ethyl sulfate was distilled off underreduced pressure to obtain 0.9 g of the aimed compound (physicalproperties unmeasurable) as a yield of 78%.

EXAMPLE 6 Preparation of methyl2-[[4,6-dimethoxypyrimidin-2-yl)oxy]-6-(hydroxyiminomethyl)benzoate(Compound No. 19)

2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate,0.8 g of hydroxyamine hydrochloride, 1.1 g of potassium acetate and 10ml of methanol were placed in a 50 ml eggplant type flask, and werestirred for 10 minutes at room temperature. Methanol was distilled offunder reduced pressure, and the residue was dissolved in ethyl acetate.The organic layer was washed with water, 5% hydrochloric acid and asaturated salt aqueous solution, and was dried with magnesium sulfateanhydride. After filtering, a small amount of Florisil was added to theresultant product, and was stirred for 5 minutes. The Florisil wasfiltered out, and ethyl acetate was distilled off under reduced pressureto obtain 1.5 g of the aimed compound (refractive index=1.5558) at ayield of 72%.

EXAMPLE 7 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[(1-ethoxycarbonylethyl)oxyiminomethyl)benzoate(Compound No. 22)

2.0 g of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoate, 3 mlof ethyl 2-bromopropionate and 0.9 g of silver oxide (I) were place in a50 ml eggplant type flask, and were allowed to stand for one night atroom temperature. 10 ml of acetone and 10 g of silica gel were added tothe resultant reaction liquor, and the acetone was distilled off underreduced pressure. The resultant product was purified by columnchromatography to obtain 0.7 g of the aimed compound (refractiveindex=1.5261) at a yield of 27%.

REFERENCE EXAMPLE 3 Preparation of methyl6-[1-(N-methoxyimino)-ethyl]salicylate (Intermediate product No. 21)

1.2 g of methyl 6-acetyl salicylate, 1;3 g of methoxyamine hydrochlorideand 1.5 g of potassium acetate were added to 30 ml of methanol, and werestirred for one night at room temperature. After completing thereaction, the reaction liquor was poured into water, and was made aceticwith hydrochloric acid to extract the reaction product with ethylacetate. The reaction product was washed with sodium hydrogencarbonateaqueous solution and water in sequence, and was dried to obtain aconcentrated oily product. The product was then purified by columnchromatography to obtain 1.15 g of the aimed compound (refractiveindex=1.5423) at a yield of 83%.

EXAMPLE 8 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(N-methoxyimino)ethyl]benzoate(Compound No. 9)

1.15 g of methyl 6-[1-(N-methoxyimino)ethyl]-salicylate, 1.12 g of4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.71 g of potassiumcarbonate were added to 50 ml of DMF, and were heated at 100° C. for 2hours. After allowing to cool, the reaction liquor was poured intowater, and was extracted with ethyl acetate. After washing the extractedproduct with water, the resultant prod0ct was dried and concentrated toobtain a crude crystal of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(N-methoxyimino)ethylbenzoate. This product was then washed with diisopropyl ether to obtain1.35 g of the aimed compound (melting point=105 to 106° C.) at a yieldof 73%.

REFERENCE EXAMPLE 4 Preparation of methyl2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoate (Intermediateproduct No. 13)

1.0 g of methyl 6-acetylsalicylate was added to a suspension solution of0.23 g of sodium hydride and 30 ml of benzene, and the resultant mixturewas stirred for 10 minutes at room temperature. 0.95 g of2-chloro-4,6-dimethoxytriazine was added to the resultant mixture, andthe mixture was stirred for one day and one night at room temperature.After completing the reaction, the reaction liquor was poured intowater, and was extracted with ethyl acetate. The extracted product waswashed with water, dried and concentrated to obtain a crystal. Theproduct thus obtained was purified by column chromatography to obtain1.15 g of the aimed compound (melting point=151° to 156° C.) at a yieldof 67%.

EXAMPLE 9 Preparation of methyl2-[(4,6-dimethoxytriazin-2-y1)oxy]-6-[1-(N-methoxyimino)ethyl]benzoate(Compound No. 41)

0.9 of methyl 2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoate, 0.68g of methoxyamine hydrochloride and 0.80 g of potassium acetate wereadded to 30 ml of methanol, and the resultant mixture was stirred forone day and one night at room temperature. The resultant reaction liquorwas poured into water, and was extracted with ethyl acetate. Afterwashing the extracted product with water, the washed product was driedand concentrated to obtain an oily product. This was then purified bycolumn chromatography to obtain 0.47 g of the aimed compound (meltingpoint=131° to 135° C.) at a yield of 48%.

EXAMPLE 10 Preparation of2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(N-methoxyimino)ethyl]benzoate(Compound No. 1)

1.5 g of benzyl ester of2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[(1-(N-methoxyimino)ethyl]benzoicacid (Compound No. 4) prepared in the same manner as in Example 1 and0.15 g of 10% palladium carbon were added to 50 ml of methanol, and 83ml of hydrogen was added to the resultant mixture with stirring at roomtemperature. After completing the reaction, palladium carbon wasfiltered out, and the solvent was distilled off under reduced pressure.An oily product thus obtained was purified by column chromatographyusing hexane/ethyl acetate as a developing solvent to obtain 1.1 g ofthe aimed compound (melting point =125° to 127° C.) at a yield of 86%.

EXAMPLE 11 Preparation of ethyl2-[(4,6-dimethoxy-2-y1)oxy]-6-[1-(N-methoxyimino)ethyl]benzoate(Compound No. 15)

2 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(Nmethoxyimino)ethyl]benzoate obtained in Example 8 was added to 50 ml ofDMF, and was fully stirred at room temperature. 0.23 g of sodium hydridewas added to the resultant liquor, and 1 g of ethyl bromide wad addedthereto after the generation of hydrogen stopped. The resultant mixturewas stirred for one hour at 60° C. The reaction liquor was then pouredinto a cold water, and an oily product thus formed was extracted withethyl acetate. The extracted oily product was washed with water, driedand concentrated. The residue oily product was purified by columnchromatography using hexane/isopropyl ether (10:1) as a developingsolvent to obtain 1.5 g of the aimed compound (melting point=65° to 68°C.) at a yield of 69%.

EXAMPLE 12 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-1-N-ethoxyimino)ethyl]benzoate(Compound No. 11)

1.0 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate,1.18 g of ethoxyamine hydrochloride and 1.18 g of potassium acetate wereadded to 30 ml of methanol, and the resultant mixture was refluxed withstirring for 5 hours. The reaction mixture was then poured into a coldwater, and was extracted with ethyl acetate. The organic layer thusformed was washed with firstly dilute hydrochloric acid, then aqueoussolution of sodium hydrogencarbonate and water in sequence. The organiclayer was then dried and concentrated to obtain a solid. The solidproduct thus obtained was washed with n-hexane to obtain 0.76 g of theaimed compound (melting point=93° to 95° C.) at a yield of 67% as acolorless transparent crystal.

EXAMPLE 13 Preparation of methyl2-[1-(N-allyloxyimino)ethyl]-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate(Compound No. 14)

1.0 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate,1.0 g of allyloxyamine hydrochloride and 0.9 g of potassium acetate wereadded to 30 ml of methanol, and were refluxed with stirring for 5 hours.The reaction mixture was then poured into a cold water, and wasextracted with ethyl acetate. The organic layer thus formed was washedwith firstly dilute hydrochloric acid, then sodium hydrogencarbonate andwater in sequence. The organic layer thus washed was then dried andconcentrated. The residue oily product was purified by columnchromatography to obtain 0.54 g of the aimed compound (melting point=76°to 78° C.) at a yield of 46% as a colorless transparent crystal.

REFERENCE EXAMPLE 5 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-propionylbenzoate (Intermediateproduct No. 17)

0.78 g of 3-hydroxy-2-methoxycarbonylpropiophenone and 0.85 g of2-methylsulfonyl-4,6-dimethoxypyrimidine were dissolved in 60 ml of DMF(dimethylformamide), and 0.15 g of sodium hydride (60% oil dispersion)was added thereto under cooling with ice. The resultant mixture wasstirred at room temperature for 8 hours, and an ice water was addedthereto. The resultant reaction liquor was extracted with ethyl acetate,and the extracted product was washed with a saturated salt aqueoussolution, and was dried with magnesium sulfate anhydride. Afterdistilling off the solvent, the mixture was purified by columnchromatography, and was crystallized with isopropyl ether to obtain 0.92g of the aimed compound (melting point=120° to 122° C.) at a yield of1.3%.

EXAMPLE 14 Preparation of methyl 6-[1-(N-methoxyimino)propyl-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (Compound No. 53)

0.62 9 of methyl 2[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-propionylbenzoate, 0.45 g ofmethoxyamine hydrochloride and 0.53 g of potassium acetate were added to80 ml of methanol, and were heat-refluxed for 6 hours. The precipitatedproduct was filtered out, and the solvent was distilled off. Water wasadded to the product, and the product was extracted with ethyl acetate.The product was then washed with water, and was dried with magnesiumsulfate anhydride. After distilling off the solvent, the mixture waspurified by column chromatography, and the purified product wascrystallized with isopropyl ether/ethyl acetate to obtain 0.60 g of theaimed compound (melting point=75° to 77° C.) at a yield of 89.5%.

EXAMPLE 15

Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)-N-formylamino-6-[1-(N-methoxyimino)ethyl]benzoate(Compound No. 131)

10 g of methyl 2 formylamino-6-[1-(N-methoxyimino)ethyl]benzoate wasadded to a solution of 1.68 g of sodium hydride in 100 ml of benzene,and the resultant mixture was stirred at room temperature for 10minutes. 8.7 g of 2-methylsulfonyl-4,6-dimethoxypyrimidine was added tothe resultant mixture, and the mixture was heat-refluxed for 6 hours.After allowing to cool, the reaction liquor was poured into an icewater, and was extracted with ethyl acetate. The organic layer thusformed was washed with water, dried and concentrated. The residue thusobtained was purified by column chromatography to obtain 8.3 g of theaimed compound (melting point=147° to 149° C.) at a yield of 54%.

EXAMPLE 16 Preparation of methyl2-[(4,6-dimethoxypyrimidin-2-yl)amino]-6-1-(N-methoxyimino)ethyl]benzoate(Compound No. 46)

1 ml of concentrated hydrochloric acid was added to a solution of 1.34 gof methyl2-[(4,6-dimethoxypyrimidin-2-yl)-N-formylamino]-6-[1-(N-methoxyimino)ethyl]benzoatein 50 ml of methanol, and the mixture was allowed to stand at roomtemperature for one night. The reaction liquor was poured into an icewater, and was extracted with ethyl acetate. The organic layer thusformed was washed with sodium hydrogencarbonate aqueous solution andwater in sequence, and was dried and concentrated. The residue thusobtained was purified by column chromatography to obtain 0.87 g of theaimed compound (melting point=82° to 84° C.) at a yield of 70%.

The herbicidal composition of the present invention comprises thepyrimidine or triazine derivative of the present invention of thegeneral formula [I]and its salt as an effective ingredient.

When the compound of the present invention is applied as a herbicide topaddy field, upland field, fruit garden, non-agricultured land or thelike, the effective ingredient may be applied in various formulationsdepending on its use object.

Generally, the herbicide of the present invention may be used as it isor may be formulated in various formulations which are commonly used asherbicidal compositions, such as a wettable powder, a granule, anemulsifiable concentrate or a dust by blending it with an inert liquidor solid carrier, a surfactant, a dispersing agent or an adjuvant whichis commonly employed for the formulation of agricultural chemicals.

As the carrier to be used for the formulation, there may be mentioned asolid carrier such as Jeeklight, talc, bentonite, clay, kaolin,diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand,ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol,xylene, cyclohexanone or methyl naphthalene. As the surfactant anddispersing agent, there may be mentioned, for example, analcohol-sulfuric acid ester, an alkylaryl sulfonate, lignin sulfonate, apolyoxyethylene glycol ether, a polyoxyethylene alkyl aryl ether or apolyoxyethylene sorbitol mono-alkylate. As the adjuvant, for example,carboxymethylcellulose, polyethylene glycol or gum arabic may bementioned. The herbicide may be diluted to a suitable concentrationbefore application, or may directly be applied.

The compound of the present invention is generally used in an amount of1 g to 10 kg/ha, preferably 1 g to 5 kg/ha, more preferably 10 g to 500g/ha as an active ingredient.

The proportion of the compound of the present invention in theformulation may vary depending upon the type of the formulation, theapplication method, the application site, timing, etc. Therefore, it cannot generally be defined. However, it is usually from 1 to 0%,preferably 10 to 20% by weight in a wettable powder, from 0.1 to 90%,preferably 0.5 to 40% by weight in an emulsifiable concentrate, from0.01 to 10%, preferably 0.1 to 1% by weight in a granule.

The herbicide is capable of controlling various weeds in a paddy fieldby irrigated soil treatment before or after the emergence of weeds or byfoliage treatment.

Further, the herbicide of the present invention :s capable ofcontrolling various weeds in an agricultural field such as an uplandfield or an orchard, or in a forest, a lawn or other non-agriculturalfield by soil treatment before or after the emergence of weeds or byfoliage treatment.

For soil treatment, the herbicide of the present invention is applied ina dose of from 1 g to 10 kg, 10 preferably from 1 g to 5 kg, morepreferably from 10 g to 500 g, of the active ingredient per ha. Forfoliage treatment, it is diluted to a concentration of from 1 to 10,000ppm for application. Most preferably, it is applied in a dose of from10.to 100 g of the active ingredient per ha for a paddy field, in a doseof from 500 g to 1 kg for a non-agricultured field.

If desired, the compound of the present invention may be used incombination with insecticides, sterilizers, other herbicides, plantgrowth controlling agents, fertilizers or the like.

Examples of other known herbicides usable in combination with thecompound of the present invention include 4-nitrophenyl2,4,6-trichlorophenyl ether (chlornitrofen), 2,4-dichlorophenyl3-methoxy-4-nitrophenyl ether (chlomethoxynil), methyl5-(2,4-dichlorophenoxy)-2-nitrobenzoate (bifenox), S-4-chlorobenzyldiethylthiocarbamate (thiobencarb), S-ethylperhydroazepin-1-carbothioate (molinate), S-1-methyl-1-phenylethylpiperidine-1-carbothioate (dimepiperate),S-benzyl-N-(1,2-dimethylpropyl)-N-ethylthiocarbamate (esprocarb),O-(3-tert-butylphenil)N-(6-methoxy-2-pyrizyl)-N-methyl-thiocarbamate(pyributycarb), methyl 3,4-dichlorophenylcarbamate (swep),O,O-diisopropyl S-(2-phenylsulfonylaminoethyl)phosphorodithioate(bensulide), S-2-methylpiperidinocarbonylmethyl O,O-dipropylphosphorodithioate (piperophos),N-(butoxymethyl)-2-chloro-2',6'-diethylacetanilide (butachlor),2-chloro-2',6'-diethyl-N-(2-propoxyethyl)acetanilide (pretilachlor),2-(benzothiazol-2-yloxy)-N-methyl-acetanilide (mefenacet),(RS)-2-bromo-3,3-dimethyl-N-(α,α-dimethylbenzyl)butyramide(bromobutide), (2,4-dichlorophenoxy)acetic acid (2,4-D) and 2,4-D ethylester, 4-chloro-o-tolyloxyacetic acid (MCPA) and MCPA ethyl ester,S-ethyl 4-chloro-o-tolyloxythioacetate (MCPA-thioethyl),4-(4-chloro-o-tolyloxy)butyric acid (MCPB),2-(2-naphthyloxy)propionanilide (naproanilide),2-(22,4-dichloro-3-methylphenoxy)propionanilide (clomeprop),2-(1,2-dimethylpropylamino)-4-ethylamino-6-methylthio-1,3,5-triazine(dimethametryn), 2,4-bis(ethylamino)-6-methylthio-1,3,5-triazine(simetryn), 2,4-bis(isopropylamino)-6-methylthio-1,3,5-triazine(prometryn), 1-(α,α-dimethylbenzyl)-3-(p-tolyl)urea (dymrone),5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazole-2(3H)-one(oxadiazon), 4-(2,4-dichlorobenzoil)-1,3-dimethyl-5-pyrazolylp-toluenesulfonate (pyrazolate),2-[4-(2,4-dichloro-3-methylbenzoil)-1,3-dimethylpyrazol-5-yloxy]-4-methylacetophenone(benzofenap),2-[4-(2,4-dichlorobenzoil-1,3-dimethylpyrazol-5-yloxy)acetophenon(pyrazoxyfen), 3-isopropyl-1H-2,1,3-benzothiadiazine-4(3H)-one2,2-dioxide (bentazone), methyl2-[[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]methyl]benzoate(bensulfuron-methyl),ethyl-5-[3-(4,6-dimethoxypyrimidin-2-yl)ureidesulfonyl]-1-methylpyrazol-4-carboxylate(pyrazosulfuron-ethyl) and the like.

Now, Formulation Examples for the herbicidal composition of the presentinvention will be given. However, it should be understood that thepresent invention is by no means restricted to these specificFormulation Examples. In this Examples, "part" means "part by weight".

FORMULATION EXAMPLE 1 (wettable powder)

10 Part of Compound No. 11, 0.5 part of Emulgen 810 (trademark, KaoCorporation), 0.5 part of Demol N (trademark, Kao Corporation), 20 partsof Kunilite 201 (trademark, Kunimine Kogyo K. K.) and 69 parts ofJeeklite CA (trademark, Jeeklite Company Ltd.) were uniformly mixed andpulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2 (wettable powder)

10 Parts of Compound No. 14, 0.5 part of Emulgen 810, 0.5 part of DemolN, 20 parts of Kunilite 201, 5 parts of Carplex 80 and 64 parts ofJeeklite CA were uniformly mixed and pulverized to obtain a wettablepowder.

FORMULATION EXAMPLE 3 (emulsifiable concentrate)

30 Parts of Compound No. 1, 60 parts of equivalent amount mixture ofxylene and isophorone, and 10 parts of surface active agent Sorpol 800A(trademark, Toho Kagaku Kogyo K. K.) were uniformly mixed and stirred toobtain an emulsifiable concentrate.

FORMULATION EXAMPLE 4 (granule)

10 Parts of Compound No. 9, 80 parts of a bulking agent comprising a 1:3mixture of talc and bentonite, 5 parts of white carbon, 5 parts ofsurface active agent Sorpol 800A and 10 parts of water were fullykneaded to obtain a paste-like material. The paste-like material wasthen extruded through a sieve aperture of 0.7 mm in diameter, and theextruded product was dried and cut into pieces of 0.5 to 1 mm in lengthto obtain granules.

FORMULATION EXAMPLE 5 (mixed granules)

2 Parts of Compound NO. 9, 5 parts of bensulfuronmethyl, 80 parts of abulking agent comprising a 1:3 mixture of talc and bentonite, 5 parts ofwhite carbon, 5 parts of surface active agent Sorpol 800A and 10 partsof water were fully kneaded to obtain a paste-like material which wasthen extruded through a sieve aperture of 0.7 mm in diameter, dried andcut into pieces of 0.5 to 1 mm in length to obtain granules.

The compound of the present invention expressed by the general formula[I] achieves an excellent herbicidal effect at a very small dose duringa long period of time from budding to growing of annual weeds such asbarnyardgrass (Echinochloa crusgalli), flatsedge (Cyperus difformis),monochoria (Monochoria vaginalis) or the like, and perennial weeds suchas bulrush (Scirpus hotarui), Alisma canaliculatum, Sagittaria pygmaea,Cyperus serotinus, Eleocharis kuroguwai or the like grown in paddyfield. The compound of the present invention is also effective as aherbicide for various weeds such as broad leaf weeds including palesmartweed (Polygonum lapathifolium), slender amaranth (Amaranthusviridis), lambsquarters (Chenopodium album), chickweed (Stellariamedia), velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa),morningglory (Ipomea spp), common cocklebur (Xanthium strumarium) or thelike, perennial and annual yellow nutsedge family weeds including purplenutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus), greenkyllinga (Cyperus brevifolius), flatsedge (Cyperus microiria), riceflatsedge (Cyperus iria) or the like, rice family weeds includingbarnyardgrass (Echinochloa crusgalli), crabgrass (Digitariasanguinalis), green foxtail (Setaria viridis), annual bluegrass (Poaannua), johnsongrass (Sorghum halepense), water foxtail (Alopecurusaequalis), wild oat (Avena fatua) or the like.

On the other hand, the herbicides of the present invention are highlysafe to crop plants, particularly rice, wheat, barley, corn, grainsorghum, soybean, cotton, sugar beet or the like.

Now, the herbicidal activities of the present invention will bedescribed with reference to Test Examples.

Test Example 1 (Herbicidal Effect Test by Paddy Field Soil Treatment)

In a plastic pot filled with paddy field soil (surface area: 100 cm²),seeds of barnyardgrass (Ec), monochoria (Mo) and Bulrush (Sc) were sownafter puddling and leveling, and water was flooded thereon to a depth of3 cm. Next day, a wettable powder prepared in accordance withFormulation Example 1 was diluted with water, and was applied todropwise to the pot in an amount of 1 kg/ha as an active ingredient.Then, the pot was cultured in a green house, and the evaluation wasconducted on the 21st day after the treatment in accordance with thestandard as identified in the following Table 3-1. The results are shownin the following Table 4.

                  TABLE 3-1                                                       ______________________________________                                        Index No.                                                                             Herbicidal effects                                                    ______________________________________                                        0       Herbicidal effect: more than 0% and less than 10%                     1       Herbicidal effect: at least 10% and less than 30%                     2       Herbicidal effect: at least 30% and less than 50%                     3       Herbicidal effect: at least 50% and less than 70%                     4       Herbicidal effect: at least 70% and less than 90%                     5       Herbicidal effect: at least 90%                                       ______________________________________                                    

                  TABLE 3-2                                                       ______________________________________                                        Index No.                                                                             Phytotoxicity                                                         ______________________________________                                        0       Phytotoxicity: more than 0% and less than 10%                         1       Phytotoxicity: at least 10% and less than 30%                         2       Phytotoxicity: at least 30% and less than 50%                         3       Phytotoxicity: at least 50% and less than 70%                         4       Phytotoxicity: at least 70% and less than 90%                         5       Phytotoxicity: at least 90% to completely withered                    ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                   Herbicidal effect                                                  Compound No. Ec          Mo     Sc                                            ______________________________________                                         1           5           5      5                                              2           5           5      5                                              3           5           5      5                                              4           5           5      5                                              5           5           5      5                                              8           5           5      5                                              9           5           5      5                                             10           5           5      5                                             11           5           5      5                                             13           5           5      4                                             18           5           5      5                                             19           5           5      5                                             20           5           5      5                                             21           5           5      5                                             22           5           5      4                                             23           5           5      4                                             29           5           5      5                                             33           5           5      5                                             34           5           5      4                                             35           5           5      4                                             42           5           5      5                                             43           5           5      4                                             44           5           5      4                                             45           5           5      4                                             48           5           5      5                                             49           5           5      5                                             50           5           5      5                                             51           5           5      5                                             52           5           5      5                                             53           5           5      5                                             58           5           5      5                                             60           5           5      4                                             61           5           5      4                                             62           5           5      4                                             63           5           5      5                                             64           5           5      5                                             65           5           5      5                                             67           5           5      5                                             68           5           5      5                                             69           5           5      5                                             70           5           5      5                                             71           5           5      5                                             72           5           5      5                                             73           5           5      5                                             74           5           5      5                                             75           5           5      5                                             76           5           5      5                                             78           5           5      5                                             79           5           5      5                                             80           5           5      5                                             81           5           5      5                                             82           5           5      5                                             83           5           5      5                                             84           5           5      5                                             85           5           5      5                                             86           5           5      5                                             87           5           5      5                                             88           5           5      5                                             91           5           5      5                                             92           5           5      5                                             93           5           5      5                                             118          5           5      5                                             119          5           5      5                                             120          5           5      5                                             121          5           5      5                                             129          5           5      5                                             130          5           5      5                                             136          5           5      5                                             137          5           5      5                                             ______________________________________                                    

Test Example 2 (Herbicidal Effect Test by Upland Field Soil Treatment)

In a plastic pot filled with upland field soil (surface area: 120 cm²),seeds of edible barnyardgrass (Ec), pale smartweed (Po), Slenderamaranth (Am), Lambsquarters (Ch) and rice flatsedge (Cy) were sown andcovered with soil. A predetermined amount of a wettable powder preparedin accordance with Formulation Example 1 was diluted with water andapplied uniformly to the soil surface by a small-sized sprayer in anamount of 1000 l/ha so that the dose of the active ingredient was 1kg/ha. The pot was then cultured in a green house, and the evaluationwas conducted on the 21st day after the the following Table 3-1. Thecompounds listed in the following Table 5 were used as comparativeherbicides. The test results are shown in the following Table 6.

                  TABLE 5                                                         ______________________________________                                        Chemical structure   Reference                                                ______________________________________                                         ##STR102##          U.S. Pat. No. 4770691                                     ##STR103##          Agricultural and Biological Chemistry 30,9,896,                               (1966)                                                    ##STR104##          U.S. Pat. No. 4427437                                    ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                                  Herbicidal effect                                                   Compound No.                                                                              Ec       Po    Am       Ch  Cy                                    ______________________________________                                         1          5        5     5        5   5                                      2          5        5     5        5   5                                      3          5        5     5        5   5                                      4          5        5     5        5   5                                      5          5        5     5        5   5                                      6          5        5     5        5   5                                      7          5        5     5        5   5                                      8          5        5     5        5   5                                      9          5        5     5        5   5                                     10          5        5     5        5   5                                     11          5        5     5        5   5                                     12          5        5     5        5   5                                     13          5        5     5        5   5                                     14          5        5     5        5   5                                     15          5        5     5        5   5                                     16          5        5     5        5   5                                     17          5        5     5        5   5                                     18          5        5     5        5   5                                     19          5        5     5        5   5                                     20          5        5     5        5   5                                     21          5        5     5        5   5                                     24          4        5     5        5   5                                     29          5        5     5        5   5                                     30          4        5     5        5   5                                     32          5        5     5        5   5                                     33          5        5     5        5   5                                     34          5        5     5        5   5                                     35          5        5     5        5   5                                     42          5        5     5        5   5                                     43          5        5     5        5   5                                     44          5        5     5        5   5                                     45          5        5     5        5   4                                     48          5        5     5        5   5                                     49          5        5     5        5   5                                     50          5        5     5        5   5                                     51          5        5     5        5   5                                     52          5        5     5        5   5                                     53          5        5     5        5   5                                     58          5        5     5        5   5                                     60          5        5     5        5   5                                     61          5        5     5        5   5                                     63          5        5     5        5   5                                     64          5        5     5        5   5                                     65          5        5     5        5   5                                     67          5        5     5        5   5                                     68          5        5     5        5   5                                     69          5        5     5        5   5                                     70          5        5     5        5   5                                     71          5        5     5        5   5                                     72          5        5     5        5   5                                     73          5        5     5        5   5                                     74          5        5     5        5   5                                     75          5        5     5        5   5                                     76          5        5     5        5   5                                     78          5        5     5        5   5                                     79          5        5     5        5   5                                     80          5        4     5        5   5                                     81          5        5     5        5   5                                     82          5        5     5        5   5                                     83          5        5     5        5   5                                     84          5        5     5        5   5                                     85          5        5     5        5   5                                     86          5        5     5        5   5                                     87          5        5     5        5   5                                     88          5        5     5        5   5                                     89          5        5     5        5   5                                     91          5        5     5        5   5                                     92          5        5     5        5   5                                     93          5        5     5        5   5                                     118         5        5     5        5   5                                     119         5        5     5        5   5                                     120         5        5     5        5   5                                     121         5        5     5        5   5                                     129         5        5     5        5   5                                     130         5        5     5        5   5                                     136         5        5     5        5   5                                     (A)         3        4     4        5   5                                     (B)         1        0     3        2   1                                     (C)         2        3     5        5   0                                     ______________________________________                                    

Test Example 3 (Herbicidal Effect Test by Upland Field FoliageTreatment)

In a plastic pot filled with upland soil (surface area: 120 cm²), seedsof edible barnyardgrass (Ec), pale smartweed (Po), slender amaranth(Am), lambsquarters (Ch) and rice flatsedge (Cy) were sown, and werecultured in a green house for 2 weeds. A predetermined amount of awettable powder prepared in accordance with Formulation Example 1 wasdiluted with water, and applied by a small-sized sprayer onto thefoliage in an amount of 1000 l/ha so that the dose of the activeingredient was 1 kg/ha. The plants were cultured in the green house, andthe evaluation was conducted on the 14th day after the treatment inaccordance with the standard as identified in the following Table 3-1.The compounds listed in the above Table 5 were used as comparativeherbicides. The test results are shown in the following Table 7.

                  TABLE 7                                                         ______________________________________                                                  Herbicidal effect                                                   Compound No.                                                                              Ec       Po    Am       Ch  Cy                                    ______________________________________                                         1          5        5     5        5   5                                      2          5        5     5        5   5                                      3          5        5     5        5   5                                      4          5        5     5        5   5                                      5          5        5     5        5   5                                      6          5        5     5        5   5                                      7          5        5     5        5   5                                      8          5        5     5        5   5                                      9          5        5     5        5   5                                     10          5        5     5        5   5                                     11          5        5     5        5   5                                     12          5        5     5        5   5                                     13          5        4     5        5   5                                     14          5        5     5        5   5                                     15          5        5     5        5   5                                     16          5        5     5        5   5                                     17          5        5     5        5   5                                     18          5        5     5        5   5                                     19          5        5     5        5   5                                     20          5        5     5        5   5                                     21          5        5     5        5   5                                     24          4        5     5        5   4                                     29          5        5     5        5   5                                     30          5        5     5        5   5                                     33          5        5     5        5   5                                     35          5        5     5        5   5                                     42          5        5     5        5   5                                     43          5        5     5        5   5                                     44          5        5     5        5   5                                     45          5        5     5        5   5                                     48          5        5     5        5   5                                     49          5        5     5        5   5                                     51          5        5     5        5   5                                     52          5        5     5        5   5                                     58          5        5     5        5   4                                     60          5        5     5        5   4                                     61          5        5     5        5   5                                     63          5        5     5        5   5                                     64          5        5     5        5   5                                     65          5        5     5        5   5                                     67          5        5     5        5   5                                     68          5        5     5        5   5                                     69          5        5     5        5   5                                     70          5        5     5        5   5                                     71          5        5     5        5   5                                     72          5        5     5        5   5                                     73          5        5     5        5   5                                     74          5        5     5        5   5                                     75          5        5     5        5   5                                     76          5        5     5        5   5                                     78          5        5     5        5   5                                     79          5        5     5        5   5                                     80          5        4     5        5   5                                     81          5        5     5        5   5                                     82          5        5     5        5   5                                     83          5        5     5        5   5                                     84          5        5     5        5   5                                     85          5        5     5        5   5                                     86          5        5     5        5   5                                     87          5        5     5        5   5                                     88          5        5     5        5   5                                     89          5        5     5        5   5                                     91          5        5     5        5   5                                     92          5        5     5        5   5                                     93          5        5     5        5   5                                     118         5        5     5        5   5                                     119         5        5     5        5   5                                     120         5        5     5        5   5                                     121         5        5     5        5   5                                     129         5        5     5        5   5                                     130         5        5     5        5   5                                     136         5        5     5        5   5                                     (A)         1        3     1        3   5                                     (B)         0        0     0        0   0                                     (C)         2        3     5        5   0                                     ______________________________________                                    

Test Example 4 (Crop Selectivity Test by Paddy Field Soil Treatment)

In a Wagner pot (surface area: 1/5000 a) filled with paddy field soil,barnyardgrass (Ec), monochoria (Mo) and bulrush (Sc) were sown afterirrigating, puddling and leveling. In the pot, two pieces of paddy rice(Or) of 2.0 plastochron were transplanted to a transplanting depth of 2cm, and flooded to a water depth of 3 cm. Next day, a predeterminedamount of a wettable powder prepared in accordance with FormulationExample 1 diluted with water, and applied dropwise to the water surface.The plants were then cultured in a green house, and the evaluations ofthe herbicidal effect and phytotoxicity were conducted on the 30th dayafter the treatment in accordance with the standards as identified inTables 3-1 and 3-2. The compounds listed in the above Table 5 were usedas comparative herbicides. The results are shown in the following Table8.

                  TABLE 8                                                         ______________________________________                                                                           Phytotox-                                  Compound Dose      Herbicidal effect                                                                             icity                                      No.      (kg/ha)   Ec      Mo    Sc    Or                                     ______________________________________                                         4       0.25      5       3     3     1                                       5       1.00      5       5     5     1                                       9       0.25      5       3     3     0                                      10       0.25      5       3     3     0                                      11       0.25      5       4     3     1                                      13       1.00      5       5     3     1                                      20       0.25      5       5     4     1                                      21       0.25      5       4     4     0                                      23       0.25      5       5     3     0                                      30       1.00      5       5     3     1                                      33       1.00      5       5     5     1                                      35       0.25      5       5     3     0                                      43       0.25      5       5     3     0                                      50       1.00      5       5     5     0                                      62       0.25      5       5     3     0                                      78       0.25      5       5     5     0                                      79       0.25      5       5     5     0                                      80       0.25      5       5     5     0                                      91       1.00      5       5     5     0                                      93       1.00      5       5     5     0                                      (A)      1.00      0       0     0     2                                      (B)      1.00      0       0     0     0                                      (C)      1.00      5       5     3     5                                      ______________________________________                                    

Test Example 5 (Crop Selectivity Test by Upland Field Soil Treatment)

In a plastic pot (surface area: 600 cm²) filled with upland field soil,soybean (Gl), cotton (Go), edible barnyardgrass (Ec), johnsongrass (So),water foxtail (Al), pale smartweed (Po), slender amaranth (Am) andlambsquarters (Ch) were sown and covered with soil. Next day, apredetermined amount of a wettable powder prepared in accordance withFormulation Example 1 was diluted with water, and applied uniformly ontothe soil surface by a small-sized sprayer in an amount of 1000 l/ha. Theplants were then cultured in a green house, and the evaluations of theherbicidal effect and phytotoxicity were conducted on the 21st day afterthe treatment in accordance with the standards as identified in Tables3-1 and 3-2. The compounds listed in the above Table 5 were used ascomparative herbicides. The results are shown in the following Table 9.

                  TABLE 9                                                         ______________________________________                                                                           Phytotox-                                  Compound                                                                              Dose     Herbicidal effect icity                                      No.     (kg/ha)  Ec    So  Al   Po  Am   Ch  Gl   Go                          ______________________________________                                         4      0.063    4     5   5    5   5    4   1    0                            9      0.25     5     5   5    5   5    5   0    0                           10      0.063    5     5   5    5   5    5   0    1                           11      0.25     5     5   5    5   5    5   2    0                           20      0.063    5     5   4    5   5    5   1    0                           21      0.063    5     5   5    5   5    5   1    0                           33      0.063    5     5   5    5   5    5   1    0                           34      0.063    5     5   4    5   5    4   0    0                           50      0.25     5     4   4    4   5    5   1    0                           51      0.063    5     4   4    4   5    4   0    0                           (A)     0.25     0     0   1    2   2    1   0    0                           (B)     0.25     0     0   0    0   1    1   0    0                           (C)     0.25     0     0   1    1   3    3   0    0                           ______________________________________                                    

Test Example 6 (Crop Selectivity Test by Upland Field Foliage Treatment)

In a plastic pot (surface area 600 cm²) filled with upland field soil,rice (Or), cotton (Co), edible barnyardgrass (Ec), pale smartweed (Po),slender amaranth (Am) and lambsquarters (Ch) were sown and were culturedin a green house for 2 weeks. A predetermined amount of a wettablepowder prepared in accordance with amount of Example 1 was diluted withwater, and applied onto the foliage by a small-sized sprayer. The plantswere then cultured in the green house, and the evaluations or theherbicidal effect and phytotoxicity were conducted on the 14th day aftertreatment. The compounds listed in the above Table 5 were used ascomparative herbicides. The results are shown in the following table 10.

                  TABLE 10                                                        ______________________________________                                                                           Phytotox-                                  Compound                                                                              Dose     Herbicidal effect icity                                      No.     (kg/ha)  Ec    So  Al   Po  Am   Ch  Gl   Go                          ______________________________________                                         5      0.063    4     4   5    4   5    5   0    0                            6      0.25     5     5   5    5   5    5   0    1                            7      0.25     5     5   5    5   5    5   0    0                           12      0.063    5     5   4    5   5    5   0    2                           13      0.25     5     5   5    5   5    5   0    1                           14      0.063    5     5   5    5   5    5   0    0                           33      0.25     5     4   5    5   5    5   1    0                           52      0.063    4     5   5    5   5    5   1    1                           (A)     0.25     3     2   0    4   2    1   0    2                           (B)     0.25     0     0   0    0   0    1   1    0                           (C)     0.25     1     0   0    1   3    3   1    1                           ______________________________________                                    

Test Example 7 (Herbicidal Effect Test for Combination Use of Herbicidesby Paddy Field Soil Treatment)

In a concrete pot (surface area: 1/400 a) filled with paddy field soil,barnyardgrass (Ec), monochoria (Mo), bulrush (Sc), flatsedge (Cy) andLindernia pyxidaria (Li) were sown and tubers of Sagittaria pygmaea (Sa)and Cyperus serotinus (Cs) were placed. In the pot, 8 pieces of rice(Or) or 2.0 plastochron were further transplanted to a transplantingdepth of 2 cm, and flooded to a water depth of 4 cm. Next day, apredetermined amount of mixed granules prepared in accordance withFormulation Example 5 were uniformly applied thereto. The plants werethen cultured outdoor, the evaluations of herbicidal effect andphytotoxicity were conducted on the 61st day after the treatment. Inaccordance with the standards as identified in the above Tables 3-1 and2-2. The results are shown in the following Table 11.

                  TABLE 11                                                        ______________________________________                                        Compound                                                                      No.                                Phytotox-                                  +       Dose      Herbicidal effect                                                                              icity                                      Sample  (kg/ha)   Ec    Mo   Sc  Cy  Li  Sa  Cs   Or                          ______________________________________                                        Compound                                                                              0.02 + 0.05                                                                             5     5    5   5   5   5   4    0                           No. 9                                                                          +                                                                            bensulfron-                                                                           0.04 + 0.1                                                                              5     5    5   5   5   5   5    0                           methyl                                                                        ______________________________________                                    

What is claimed is:
 1. A triazine derivative or its salt, said triazinederivative having the formula: ##STR105## wherein R represents a groupof the formula OR³ {wherein R³ represents a hydrogen atom, a C₁₋₈ alkylgroup (which may be substituted with a halogen atom, a nitro group, acyano group, a C₁₋₈ alkoxy group, a C₁₋₈ alkylthio group, a C₁₋₈alkylsulfinyl group, a C₁₋₈ alkylsulfonyl group, a phenylthio group, aphenylsulfinyl group, a phenylsulfonyl group, a benzyloxy group, anR'COO-- group (R'═C₁₋₈ alkyl), a C₁₋₈ alkoxycarbonyloxy group, anN,N-di-C₁₋₄ -alkylamino group or a phthalimidoyl group), a C₂₋₈ alkenylgroup, a halogen-substituted C₂₋₈ alkenyl group, a C₂₋₈ alkynyl group, ahalogen-substituted C₂₋₈ alkynyl group, a phenyl group (which may besubstituted with a halogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxygroup), a benzyl group (which may be substituted with a halogen atom, aC₁₋₈ alkyl group or a C₁₋₈ alkoxy group), a C₁₋₄ alkylideneamino group,a C₄₋₆ cycloalkylideneamino group, a group of the formula ##STR106##(wherein R⁴ represents a hydrogen atom or a C₁₋₃ alkyl group, R⁵represents a C₁₋₈ alkyl group, a phenyl group (which may be substitutedwith a halogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group), anamino group, a C₁₋₈ alkylamino group or a di-C₁₋₄ -alkylamino group, andn represents an integer of 1 to 3) an alkali metal atom, an alkalineearth metal atom or an organic amino cation}; a group of the formula SR⁶{wherein R⁶ represents a hydrogen atom, a C₁₋₈ alkyl group, a phenylgroup (which may be substituted with a halogen atom, a C₁₋₆ alkyl groupor a C₁₋₆ alkoxy group), a benzyl group (which may be substituted with ahalogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group), a C₂₋₈ alkenylgroup, a halogen-substituted C₂₋₈ alkenyl group, a C₂₋₈ alkynyl group ora halogen-substituted C₂₋₈ alkynyl group}; a group of the formula##STR107## {wherein R⁷ and R⁸ may be the same or different and representa hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈ alkoxy group or a phenylgroup (which may be substituted with a halogen atom, a C₁₋₆ alkyl groupor a C₁₋₆ alkoxy group )}; or an imidazolyl group;R¹ represents ahydrogen atom, a C₁₋₈ alkyl group (which may be substituted with ahalogen atom, a C₁₋₈ alkoxy group, a C₁₋₈ alkylthio group, a C₁₋₈alkylsulfinyl group, a C₁₋₈ alkylsulfonyl group, an R"CO-- group(R"═C₁₋₆ alkyl, phenyl or benzyl) or a cyano group), a phenyl group(which may be substituted with a halogen atom, a C₁₋₆ alkyl group or aC₁₋₆ alkoxy group) or a benzyl group (which may be substituted with ahalogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group); R² representsa hydroxyl group, a C₁₋₈ alkyl group (which may be substituted with oneor two halogen atoms, a C₂₋₈ alkoxyalkyl group, a C₂₋₈ alkenyl group, AC₂₋₈ alkynyl group, a C₁₋₈ alkoxy group (which may be substituted with ahalogen atom, a benzyloxy group, a C₁₋₈ alkoxycarbonyl group, a C₃₋₇cycloalkyl group, an R"CO-- group (R"═C₁₋₆ alkyl, phenyl or benzyl), anN,N-di-C₁₋₄ -alkylamino group or a C₁₋₈ alkoxy group), a phenyl group(which may be substituted with a halogen atom, a C₁₋₄ alkyl group or aC₁₋₄ alkoxy group), a phenoxy group (which may be substituted with ahalogen atom, a C₁₋₄ alkyl group or a C₁₋₄ alkoxy group), a C₂₋₈alkenyloxy group (which may be substituted with one or two halogen atomsor a phenyl group), a C₂₋₈ alkynyloxy group (which may be substitutedwith one or two halogen atoms or a phenyl group), a benzyloxy group(which may be substituted with a halogen atom, a C₁₋₄ alkyl group or aC₁₋₄ alkoxy group), a trimethylsilyloxy group, a C₃₋₇ cycloalkoxy group,a group of the formula ##STR108## {wherein R⁹ represents a C₁₋₈ alkylgroup which may be substituted with a halogen atom, a C₃₋₇ cycloalkylgroup, a phenyl group (which may be substituted with a halogen atom, aC₁₋₄ alkyl group or a C₁₋₄ alkoxy group), a C₁₋₈ alkoxy group or a groupof the formula: ##STR109## (wherein R⁷ and R⁸ are as defined above)}, agroup of the formula ##STR110## (wherein X represents a halogen atom, aC₁₋₄ alkyl group or a C₁₋₄ alkoxy group, n represents an integer of 1 to3 and R⁴ is as defined above), a phenylamino group, a C₁₋₄alkoxycarbonylamino group or a C₁₋₄ alkylcarbonylamino group; A and Bmay be the same or different and represent a C₁₋₄ alkyl group, a C₁₋₄alkoxy group, a halogen atom, a halogen-substituted C₁₋₄ alkyl group, ahalogen-substituted C₁₋₄ alkoxy group or a di-C₁₋₄ -alkylamino group; Yrepresents an oxygen atom, a sulfur atom, an --NH-- group of a group ofthe formula ##STR111## (wherein R¹⁰ represents a hydrogen atom, a C₁₋₈alkyl group or a C₁₋₈ alkyl group or a C₁₋₈ alkoxy group); and Zrepresent a nitrogen atom.
 2. The triazine derivative or its saltaccording to claim 1, wherein Y is an oxygen atom or a sulfur atom. 3.The triazine derivative or its salt according to claim 1, wherein Y isan --NH-- group or a group of the formula: ##STR112## (wherein R¹⁰represents a hydrogen atom, a C₁₋₈ alkyl group or a C₁₋₈ alkoxy group).4. A method for controlling weeds, which comprises applying aherbicidally effective amount of the compound of claim 1 to the locus ofweed growth.
 5. A herbicidal composition comprising:a herbicidallyeffective amount of a triazine derivative or its salt, said triazinederivative having the general formula ##STR113## wherein R represents agroup of the formula OR³ {wherein R³ represents a hydrogen atom, a C₁₋₈alkyl group (which may be substituted with a halogen atom, a nitrogroup, a cyano group, a C₁₋₈ alkoxy group, a C₁₋₈ alkylthio group, aC₁₋₈ alkylsulfinyl group, a C₁₋₈ alkylsulfonyl group, a phenylthiogroup, a phenylsulfinyl group, a phenylsulfonyl group, a benzyloxygroup, an R'COO-- group (R'═C₁₋₈ alkyl), a C₁₋₈ alkoxycarbonyloxy group,an N,N-di-C₁₋₄ -alkylamino group or a phthalimidoyl group), a C₂₋₈alkenyl group, a halogen-substituted C₂₋₈ alkenyl group, a C₂₋₈ alkynylgroup, a halogen-substituted C₂₋₈ alkynyl group, a phenyl group (whichmay be substituted with a halogen atom, a C₁₋₆ alkyl group or a C₁₋₆alkoxy group), a benzyl group (which may be substituted with a halogenatom, a C₁₋₈ alkyl group or a C₁₋₈ alkoxy group), a C₁₋₄ alkylideneaminogroup, a C₄₋₆ cycloalkylideneamino group, a group of the formula##STR114## (wherein R⁴ represents a hydrogen atom or a C₁₋₃ alkyl group,R⁵ represents a C₁₋₈ alkyl group, a phenyl group (which may besubstituted with a halogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxygroup), an amino group, a C₁₋₈ alkylamino group or a di-C₁₋₄ -alkylaminogroup, and n represents an integer of 1 to 3) an alkali metal atom, analkaline earth metal atom or an organic amine cation}; a group of theformula SR⁶ {wherein R⁶ represents a hydrogen atom, a C₁₋₈ alkyl group,a phenyl group (which may be substituted with a halogen atom, a C₁₋₆alkyl group or a C₁₋₆ alkoxy group), a benzyl group (which may besubstituted with a halogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxygroup), a C₂₋₈ alkenyl group, a halogen-substituted C₂₋₈ alkenyl group,a C₂₋₈ alkynyl group or a halogen-substituted C₂₋₈ alkynyl group}; agroup of the formula ##STR115## {wherein R⁷ and R⁸ may be the same ordifferent and represent a hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈alkoxy group or a phenyl group (which may be substituted with a halogenatom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group)}; or an imidazolylgroup; R¹ represents a hydrogen atom, a C₁₋₈ alkyl group (which may besubstituted with a halogen atom, a C₁₋₈ alkoxy group, a C₁₋₈ alkylthiogroup, a C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkylsulfonyl group, an R"CO--group (R"═C₁₋₆ alkyl, phenyl or benzyl) or a cyano group), a phenylgroup (which may be substituted with a halogen atom, a C₁₋₆ alkyl groupor a C₁₋₆ alkoxy group) or a benzyl group (which may be substituted witha halogen atom, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group); R²represents a hydroxyl group, a C₁₋₈ alkyl group (which may besubstituted with one or two halogen atoms), a C₂₋₈ alkoxyalkyl group, aC₂₋₈ alkenyl group, a C₂₋₈ alkynyl group, a C₁₋₈ alkoxy group (which maybe substituted with a halogen atom, a benzyloxy group, a C₁₋₈alkoxycarbonyl group, a C₃₋₇ cycloalkyl group, an R"CO-- group (R"═C₁₋₆alkyl, phenyl or benzyl), an N,N-di-C₁₋₄ -alkylamino group or a C₁₋₈alkoxy group), a phenyl group (which may be substituted with a halogenatom, a C₁₋₄ alkyl group or a C₁₋₄ alkoxy group), a phenoxy group (whichmay be substituted with a halogen atom, a C₁₋₄ alkyl group or a C₁₋₄alkoxy group), a C₂₋₈ alkenyloxy group (which may be substituted withone or two halogen atoms or a phenyl group), a C₂₋₈ alkynyloxy group(which may be substituted with one or two halogen atoms or a phenylgroup), a benzyloxy group (which may be substituted with a halogenatom), a C₁₋₄ alkyl group or a C₁₋₄ alkoxy group), a trimethylsilyloxygroup, a C₃₋₇ cycloalkoxy group, a group of the formula ##STR116##{wherein R⁹ represents a C₁₋₈ alkyl group (which may be substituted witha halogen atom), a C₃₋₇ cycloalkyl group, a phenyl group (which may besubstituted with a halogen atom, a C₁₋₄ alkyl group or a C₁₋₄ alkoxygroup), a C₁₋₈ alkoxy group or a group of the formula: ##STR117##(wherein R⁷ and R⁸ are as defined above)}, a group of the formula##STR118## (wherein X represents a halogen atom, a C₁₋₄ alkyl group or aC₁₋₄ alkoxy group, n represents an integer of 1 to 3 and R⁴ is asdefined above), a phenylamino group, a C₁₋₄ alkoxycarbonylamino group ora C₁₋₄ alkylcarbonylamino group; A and B may be the same or differentand represent a C₁₋₄ alkyl group, a C₁₋₄ alkoxy group, a halogen atom, ahalogen-substituted C₁₋₄ alkyl group, a halogen-substituted C₁₋₄ alkoxygroup or a di-C₁₋₄ -alkylamino group; Y represents an oxygen atom, asulfur atom, an --NH-- group or a group of the formula ##STR119##(wherein R¹⁰ represents a hydrogen atom, a C₁₋₈ alkyl group or a C₁₋₈group); and Z represents a nitrogen atom; andan agricultural carrier ordiluent.
 6. The composition according to claim 5, wherein Y is an oxygenatom or a sulfur atom.
 7. The composition according to claim 5, whereinY is an --NH-- group or a group of the formula ##STR120## (wherein R¹⁰represents a hydrogen atom, a C₁₋₈ alkyl group or a C₁₋₈ alkoxy group).